1-(2-azidophenyl)-3-methyl-4-phenylpent-1,2,4-triene | 905566-13-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1-(2-azidophenyl)-3-methyl-4-phenylpent-1,2,4-triene
• CAS: 905566-13-4
• 化学式: C₁₈H₁₅N₃
• 分子量: 273.337
• InChiKey: DQORJBBZCMZCHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-azidophenyl)-3-methyl-4-phenylpent-1,2,4-triene 在 silica gel 作用下， 以 乙醚 、 正己烷 、 氘代甲苯 为溶剂， 反应 0.25h， 生成 1-methyl-2-phenyl-9H-pyrrolo[1,2-a]indole
  参考文献：
  名称：

  Allenyl Azide Cycloaddition Chemistry. Synthesis of Annelated Indoles from 2-(Allenyl)phenyl Azide Substrates

  摘要：

  [GRAPHICS]Thermolysis of 2-(allenyl) phenyl azides leads to a cascade cyclization sequence furnishing both C(2)-C(3) and N-C(2) cyclopentannelated indoles.

  DOI：

  10.1021/ol061216u
• 作为产物：
  描述：

  2-叠氮基苯甲醛 在 四(三苯基膦)钯 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.33h， 生成 1-(2-azidophenyl)-3-methyl-4-phenylpent-1,2,4-triene
  参考文献：
  名称：

  Allenyl Azide Cycloaddition Chemistry. Synthesis of Annelated Indoles from 2-(Allenyl)phenyl Azide Substrates

  摘要：

  [GRAPHICS]Thermolysis of 2-(allenyl) phenyl azides leads to a cascade cyclization sequence furnishing both C(2)-C(3) and N-C(2) cyclopentannelated indoles.

  DOI：

  10.1021/ol061216u

文献信息

• Allenyl Azide Cycloaddition Chemistry. 2,3-Cyclopentennelated Indole Synthesis through Indolidene Intermediates
  作者：Ken S. Feldman、D. Keith Hester、Malliga R. Iyer、Paul J. Munson、Carlos Silva López、Olalla Nieto Faza

  DOI：10.1021/jo900659w

  日期：2009.7.17

  The thermal, photochemical, and photochemical/CuI-mediated cascade cyclizations of a range of substituted 1-(2-azidophenyl)-3-alkenylallenes are described. These reactions provide both 1,2- and 2,3-cyclopentennelated indole products in varying ratios. In most cases, high regioselectivity for the 2,3-annelated isomer can be achieved under the hv/CuI conditions. Computational studies of this multistep reaction support the intermediacy of indolidene intermediates whose electrocyclizations (with or without copper present) define the regioselectivity branch point in the sequence.
• Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved Regioselectivity
  作者：Ken S. Feldman、D. Keith Hester、Carlos Silva López、Olalla Nieto Faza

  DOI：10.1021/ol800429j

  日期：2008.4.1

  Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modestto-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.
• Allenyl Azide Cycloaddition Chemistry. Synthesis of Annelated Indoles from 2-(Allenyl)phenyl Azide Substrates
  作者：Ken S. Feldman、Malliga R. Iyer、D. Keith Hester

  DOI：10.1021/ol061216u

  日期：2006.7.1

  [GRAPHICS]Thermolysis of 2-(allenyl) phenyl azides leads to a cascade cyclization sequence furnishing both C(2)-C(3) and N-C(2) cyclopentannelated indoles.